344
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Two 8-[(Anthraquinone-2-yl)-Linked]-2′-Deoxyadenosine 3′-Benzyl Hydrogen Phosphates for Studies of Photoinduced Hole Transport in DNA

&
Pages 85-110 | Received 22 Sep 2004, Accepted 08 Nov 2004, Published online: 24 Jun 2011

References

  • Lewis , F . D .; Liu , X .; Miller , S . E .; Hayes , R . T .; Wasielewski , M . R . Dynamics of electron injection in DNA hairpins . J. Am. Chem. Soc . 2002 , 124 , 11280 – 11281 . [PUBMED] [INFOTRIEVE]
  • Lewis , F . D .; Letsinger , R . L .; Wasielewski , M . R . Dynamics of photoinduced charge transfer in synthetic DNA hairpins . Acc. Chem. Res . 2001 , 34 , 159 – 170 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Lewis , F . D .; Kalgutkar , R . S .; Wu , Y .; Liu , X .; Liu , J .; Hayes , R . T .; Miller , S . E .; Wasielewski , M . R . Driving force dependence of electron transfer dynamics in synthetic DNA hairpins . J. Am. Chem. Soc . 2000 , 122 , 12346 – 12351. [CROSSREF]
  • Lewis , F . D .; Liu , X .; Liu , J .; Miller , S . E .; Hayes , R . T .; Wasielewski , M . R . Direct measurement of hole transport dynamics in DNA . Nature 2000 , 406 , 51 – 53 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Lewis , F . D .; Wu , T .; Liu , X .; Letsinger , R . L .; Greenfield , S . R .; Miller , S . E .; Wasielewski , M . R . Dynamics of photoinduced charge separation and charge recombination in synthetic DNA hairpins with stilbenecarboxamide linkers . J. Am. Chem. Soc . 2000 , 122 , 2889 – 2902 . [CROSSREF]
  • Giese , B .; Carl , B .; Carl , T .; Carell , T .; Behrens , C .; Hennecke , U .; Shiemann , O .; Feresin , E . Excess electron transport through DNA: a single electron repairs more than one UV-induced lesion . Angew. Chem . 2004 , 116 , 1884 – 1887 . [CROSSREF]
  • Giese , B .; Spichty , M .; Wessely , S . Long-distance charge transport through DNA. An extended hopping model . Pure Appl. Chem . 2001 , 73 , 449 – 453 .
  • Giese , B .; Amaudrut , J .; Kohler , A.-K .; Spormann , M .; Wessely , S . Direct observation of hole transfer through DNA by hopping between adenine bases and by tunnelling . Nature 2001 , 412 , 318 – 320 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Meggers , E .; Dussy , A .; Schafer , T .; Giese , B . Electron transfer in DNA from guanine and 8-oxoguanine to a radical cation of the carbohydrate backbone . Chem. Eur. J . 2000 , 6 , 485 – 492 . [CROSSREF]
  • Giese , B . Long-distance charge transport in DNA: the hopping mechanism . Acc. Chem. Res . 2000 , 33 , 631 – 636 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Giese , B .; Wessely , S .; Spormann , M .; Lindemann , U .; Meggers , E .; Michel-Beyerle , M . E . On the mechanism of long-range electron transfer through DNA . Angew. Chem. Int. Ed . 1999 , 38 , 996 – 997 . [CROSSREF]
  • Barnett , R . N .; Cleveland , C . L .; Joy , A .; Landman , U .; Schuster , G . B . Charge migration in DNA: ion-gated transport . Science 2001 , 294 , 567 – 571 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Schuster , G . B . Long-range charge transfer in DNA: transient structural distortions control the distance dependence . Acc. Chem. Res . 2000 , 33 , 253 – 260 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Dotse , A . K .; Boone , E . K .; Schuster , G . B . Remote cis-syn-thymine [2 + 2] dimers are not repaired by radical cations migrating in duplex DNA . J. Am. Chem. Soc . 2000 , 122 , 6825 – 6833 . [CROSSREF]
  • Ly , D .; Sanii , L .; Schuster , G . B . Mechanism of charge transport in DNA: internally linked anthraquinone conjugates support phonon-assisted polaron hopping . J. Am. Chem. Soc . 1999 , 121 , 9400 – 9410 . [CROSSREF]
  • Henderson , P . T .; Jones , D .; Hampkin , G .; Kan , Y .; Schuster , G . B . Long-distance charge transport in duplex DNA: the phonon-assisted polaron-like hopping mechanism . Proc. Natl. Acad. Sci. U. S. A . 1999 , 96 , 8353 – 8358 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Cai , Z .; Xifeng , L .; Sevilla , M . D . Excess electron transfer in DNA: effect of base sequence and proton transfer . J. Phys. Chem. B 2002 , 106 , 2755 – 2762 . [CROSSREF]
  • Taylor , J .; Eliezer , I .; Sevilla , M . D . Proton-assisted electron transfer in irradiated DNA-acrylamide complexes: modeled by theory . J. Am. Chem. Soc . 2001 , 105 , 1614 – 1617 .
  • Cai , Z .; Gu , Z .; Sevilla , M . D . Electron spin resonance study of electron and hole transfer in DNA: effects of hydration, aliphatic amine cations, and histone proteins . J. Phys. Chem. B 2001 , 105 , 6031 – 6041 . [CROSSREF]
  • Cai , Z .; Gu , Z .; Sevilla , M . D . Electron spin resonance study of the temperature dependence of electron transfer in DNA: competitive processes of tunneling, protonation, and hopping . J. Phys. Chem. B 2000 , 104 , 10406 – 10411 . [CSA] [CROSSREF]
  • Steenken , S .; Jovanovic , S . V .; Bietti , M .; Bernhard , K . The trap depth (in DNA) of 8-Oxo-7,8-dihydro-2′-deoxyguanosine as derived from electron-transfer equilibria in aqueous solution . J. Am. Chem. Soc . 2000 , 122 , 2373 – 2374 . [CROSSREF]
  • Steenken , S . Electron transfer in DNA? Competition by ultra-fast proton transfer? . Biol. Chem . 1997 , 378 , 1293 – 1297 . [PUBMED] [INFOTRIEVE] [CSA]
  • Steenken , S .; Jovanovic , S . V . How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution . J. Am. Chem. Soc . 1997 , 119 , 617 – 618 . [CROSSREF]
  • Schuster , G . B ., Ed.; Top. Curr. Chem. , Springer-Verlag : Berlin , 2004 ; Vol. 237 , 244 .
  • Schuster , G . B ., Ed.; Top. Curr. Chem. , Springer-Verlag : Berlin , 2004 ; Vol. 236 , 219 .
  • Arkin , M . R .; Stemp , E . D.A .; Pulver , S . C .; Barton , J . K . Long-range oxidation of guanine by Ru(III) in duplex DNA . Chem. Biol . 1997 , 4 , 389 – 400 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Dandliker , P . J .; Holmlin , R . E .; Barton , J . K . Oxidative thymine dimer repair in the DNA helix . Science 1997 , 275 , 1465 – 1468 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Kelley , S . O .; Jackson , N . M .; Hill , M . G .; Barton , J . K . Long-range electron transfer through DNA films . Angew. Chem. Int. Ed . 1999 , 38 , 941 – 944 . [CROSSREF]
  • Kelley , S . O .; Barton , J . K . Electron transfer between bases in double helical DNA . Science 1999 , 283 , 375 – 381. [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Stemp , E . D.A .; Barton , J . K . The Flash-Quench technique in protein–DNA electron transfer: reduction of the guanine radical by ferrocytochrome c . Inorg. Chem . 2000 , 39 , 3868 – 3874 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Bhattacharya , P . K .; Barton , J . K . Influence of intervening mismatches on long-range guanine oxidation in DNA duplexes . J. Am. Chem. Soc . 2001 , 123 , 8649 – 8656 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Ito , T .; Rokita , S . E . Excess electron transfer from an internally conjugated aromatic amine to 5-bromo-2′-deoxyuridine in DNA . J. Am. Chem. Soc . 2003 , 125 , 11480 – 11481 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Ito , T .; Rokita , S . E . Criteria for efficient transport of excess electrons in DNA . Angew. Chem. Int. Ed . 2004 , 43 , 1839 – 1842 . [CSA] [CROSSREF]
  • Breeger , S .; Hennecke , U .; Carell , T . Excess electron-transfer-based repair of a cis-syn thymine dimer in DNA is not sequence dependent . J. Am. Chem. Soc . 2004 , 126 , 1302 – 1303 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Cichon , M . K .; Haas , C .; Grolle , F .; Mees , A .; Carell , T . Efficient interstrand excess electron transfer in PNA: DNA hybrids . J. Am. Chem. Soc . 2002 , 124 , 13984 – 13985 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Schwogler , A .; Burgdorf , L . T .; Carell , T . Self-repairing DNA based on a reductive electron transfer through the base stack . Angew. Chem. Int. Ed . 2000 , 39 , 3918 – 3920 . [CROSSREF]
  • Behrens , C .; Cichon , M . K .; Grolle , F .; Hennecke , U .; Carell , T . Excess electron transfer in defined donor-nucleobase and donor-DNA-acceptor systems . Top. Curr. Chem . 2004 , 236 , 187 – 204 .
  • Behrens , C .; Burgdorf , L . T .; Schwogler , A .; Carell , T . Weak distance dependence of excess electron transfer in DNA . Angew. Chem. Int. Ed . 2002 , 41 , 1763 – 1766 . [CROSSREF]
  • Sartor , V .; Boone , E .; Schuster , G . B . Long-distance radical cation migration through A/T base pairs in DNA: an experimental test of theory . J. Phys. Chem. B 2001 , 105 , 11057 – 11059 . [CROSSREF]
  • Abdou , I . M .; Sartor , V .; Cao , H .; Schuster , G . B . Long-distance radical cation migration in Z-form DNA . J. Am. Chem. Soc . 2001 , 123 , 6696 – 6697 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Sanii , L .; Schuster , G . B . Long-distance transport in DNA: sequence-dependent radical cation injection efficiency . J. Am. Chem. Soc . 2000 , 122 , 11545 – 11546 . [CROSSREF]
  • Sartor , V .; Henderson , P . T .; Schuster , G . B . Radical cation transport and reaction in RNA/DNA hybrid duplexes: effect of global structure on reactivity . J. Am. Chem. Soc . 1999 , 121 , 11027 – 11033 . [CROSSREF]
  • Gasper , S . M .; Armitage , B .; Shui , X .; Hu , G . G .; Yu , C .; Schuster , G . B .; Williams , L . D . Three-dimensional structure and reactivity of a photochemical cleavage agent bound to DNA . J. Am. Chem. Soc . 1998 , 120 , 12402 – 12409 . [CROSSREF]
  • Breslin , D . T .; Coury , J . E .; Anderson , J . R .; LMcFail-Isom , L .; Kan , Y .; Williams , L . D .; Bottomley , L . A .; Schuster , G . B . Anthraquinone photonuclease structure determines its mode of binding to DNA and the cleavage chemistry observed . J. Am. Chem. Soc . 1997 , 119 , 5043 – 5044 . [CROSSREF]
  • Gasper , S . M .; Schuster , G . B . Intramolecular photoinduced electron transfer to anthraquinones linked to duplex DNA: the effect of gaps and traps on long-range radical cation migration . J. Am. Chem. Soc . 1997 , 119 , 12762 – 12771 . [CROSSREF]
  • Armitage , B .; Koch , T .; Frydenlund , H .; Orum , H .; Batz , H.-G .; Schuster , G . B . Peptide nucleic acid-anthrquinone conjugates: strand invasion and photoinduced cleavage of duplex DNA . Nuc. Acids Res . 1997 , 25 , 4674 – 4678 . [CROSSREF]
  • Ly , D .; Kan , Y . Z .; Armitage , B .; Schuster , G . B . Cleavage of DNA by irradiation of substituted anthraquinones: intercalation promotes electron-transfer and efficient reaction at GG steps . J. Am. Chem. Soc . 1996 , 118 , 8747 – 8748 . [CROSSREF]
  • Nandanan , E .; Jang , S.-Y .; Moro , S .; Kim , H . O .; Siddiqui , M . A .; Russ , P .; Marquez , V . E .; Busson , R .; Herdewijn , P .; Harden , T . K .; Boyer , J . L .; Jacobson , K . A . Synthesis, biological activity, and molecular modeling of ribose-modified deoxyadenosine bisphosphate analogues as P2Y1 receptor ligands . J. Med. Chem . 2000 , 43 , 829 – 842 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Camaioni , E .; Boyer , J . L .; Mohanram , A .; Harden , T . K .; Jacobson , K . A . Deoxyadenosine bisphosphate derivatives as potent antagonists at P2Y1 . J. Med. Chem . 1998 , 41 , 183 – 190 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Nandanan , E .; Camaioni , E .; Jang , S.-Y .; Kim , Y.-C .; Cristalli , G .; Herdewijn , P .; Secrist , J . A .; Tiwari , K . N .; Mohanram , A .; Harden , T . K .; Boyer , J . L .; Jacobson , K . A . Structure-activity relationships of bisphosphate nucleotide derivatives as P2Y1 receptor antagonists and partial agonists . J. Med. Chem . 1999 , 42 , 1625 – 1638 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Efimtseva , E . V .; Shelkunova , A . A .; Mikhailov , S . N .; Nauwelaerts , K .; Rozenski , J .; Lescrinier , E .; Herdewijn , P . Synthesis and properties of phosphorylated 3′-O-β-D-ribofuranosyl-2′-deoxythymidine . Nucleosides, Nucleotides Nucleic Acids 2003 , 22 , 359 – 371 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Uchiyama , M .; Aso , Y .; Noyori , R .; Hayakawa , Y . O-selective phosphorylation of nucleosides without N-protection . J. Org. Chem . 1993 , 58 , 373 – 379. [CROSSREF]
  • Gefflaut , T .; Lemaire , M .; Valentin , M.-L .; Bolte , J . A novel efficient synthesis of dihydroxyacetone phosphate and bromoacetol phosphate for use in enzymatic aldol syntheses . J. Org. Chem . 1997 , 62 , 5920 – 5922 .
  • Koppisch , A . T .; Poulter , C . D . Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol and 2-C-methyl-D-erythritol-4-phosphate . J. Org. Chem . 2002 , 67 , 5416 – 5418 . [PUBMED] [INFOTRIEVE]
  • Armstrong , J . I .; Verdugo , D . E .; Bertozzi , C . R . Synthesis of a bisubstrate analogue targeting estrogen sulfotransferase . J. Org. Chem . 2003 , 68 , 170 – 173 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Watanabe , Y .; Komoda , Y .; Ebisuya , K .; Ozaki , S . An efficient phosphorylation method using a new phosphitylating agent, 2-diethylamino-1,3,2-benzodioxaphosphepane . Tetrahedron Lett . 1990 , 31 , 255 – 256 . [CROSSREF]
  • Giner , J.-L .; Ferris , W . V . Synthesis of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate . Org. Lett . 2002 , 4 , 1225 – 1226 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Yu , K.-L .; Fraser-Reid , B . A novel reagent for the synthesis of myo-inositol phosphates: N,N-diisopropyl dibenzyl phosphoramidite . Tetrahedron Lett . 1988 , 29 , 979 – 982 . [CROSSREF]
  • Guy , A .; Duplaa , A.-M .; Harel , P .; Teoule , R . Synthesis and characterization of DNA fragments bearing an adenine radiation product: 7,8-dihydroadenin-8-one . Helv. Chim. Acta 1988 , 71 , 1566 – 1572 . [CROSSREF]
  • Wood , M . L .; Esteve , A .; Morningstar , M . L .; Kuziemko , G . M .; Essigmann , J . M . Genetic effects of oxidative DNA damage: comparative mutagenesis of 7,8- dihydro-8-oxoguanine and 7,8-dihydro-8-oxoadenine in Escherichia coli . Nuc. Acids Res . 1992 , 20 , 6023 – 6032 .
  • Ettner , N .; Haak , U .; Niederweis , M .; Hillen , W . Synthesis of 8-bromo- and 8-azido-2′-deoxyadenosine-5′-O-(1-thiotriphosphate) . Nucleosides Nucleotides 1993 , 12 , 757 – 771 .
  • Eason , R . G .; Burkhardt , D . M .; Phillips , S . J .; Smith , D . P .; David , S . S . Synthesis and characterization of 8-methoxy-2′- deoxyadenosine-containing oligonucleotides to probe the syn glycosidic conformation of 2′-deoxyadenosine within DNA . Nuc. Acids Res . 1996 , 24 , 890 – 897 . [CROSSREF]
  • Jones , R . A . Preparation of protected deoxynucleosides . In Oligonucleotide Synthesis: A Practical Approach, , 3rd Ed .; Gait , M . J ., Ed.; Oxford University Press : New York , 1992 ; 27 – 29 .
  • Hashimoto , H .; Nelson , M . G .; Switzer , C . Zwitterionic DNA . J. Am. Chem. Soc . 1993 , 115 , 7128 – 7134 . [CROSSREF]
  • Graham , D .; Parkinson , J . A .; Brown , T . DNA duplexes stabilized by modified monomer residues: synthesis and stability . J. Chem. Soc., Perkin Trans . 1998 , 1 , 1131 – 1138 . [CROSSREF]
  • Tierney , M . T .; Grinstaff , M . W . Synthesis and stability of oligodeoxynucleotides containing C8-labeled 2′-deoxyadenosine: novel redox nucleobase probes for DNA-mediated charge-transfere studies . Org. Lett . 2000 , 2 , 3413 – 3416 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Catalanotti , B .; Galeone , A .; Gomez-Paloma , L .; Mayol , L .; Pepe , A . 2′-Deoxy-8-(propyn-1-yl)adenosine-containing pligonucleotides: effects on stability of duplex and quadruplex structures . Bioorg. Med. Chem. Lett . 2000 , 10 , 2005 – 2009 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Brossette , T .; Faou , A . L .; Goujon , L .; Valleix , A .; Creminon , C .; Grassi , J .; Mioskowski , C .; Lebeau , L . Synthesis of polyphosphorylated AZT derivatives for the development of specific enzyme immunoassays . J. Org. Chem . 1999 , 64 , 5083 – 5090 . [CROSSREF]
  • Mathieu , R .; Baurand , A .; Schmitt , M .; Gachet , C .; Bourguignon , J.-J . Synthesis and biological activity of 2-alkylated deoxyadenosine bisphosphate derivatives as P2Y1 receptor antagonists . Bioorg. Med. Chem . 2004 , 12 , 1769 – 1779 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Gaballah , S . T .; Kerr , C . E .; Eaton , B . E .; Netzel , T . L . Synthesis of 5-(2,2′-bipyridinyl and 2,2′-bipyridinediiumyl)-2′-deoxyuridine nucleosides: precursors to Metallo-DNA conjugates . Nucleosides, Nucleotides Nucleic Acids 2002 , 21 , 547 – 560 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Gaballah , S . T .; Netzel , T . L . Synthesis of 5-(pyridinyl and pyridiniumyl)-2′-deoxyuridine nucleosides: reversible electron traps for DNA . Nucleosides Nucleotides Nucleic Acids 2002 , 21 , 681 – 694 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Atkinson , T .; Smith , M . Solid-phase synthesis of oligodeoxyribonucleotides by the phosphite-triester method . In Oligonucleotide Synthesis: A Practical Approach, , 3rd Ed .; Gait , M . J ., Ed.; Oxford University Press : New York , 1992 ; 49 .
  • Mirrington , R . N .; Schmalzl , K . J . Bicyclo[2.2.2]octenes. VI. Total synthesis of (+ −)-seychellene . J. Org. Chem . 1972 , 37 , 2877 – 2881 . [CROSSREF]
  • Samano , V .; Robins , M . J . Nucleic acid related compounds. 60. Mild periodinane oxidation of protected nucleosides to give 2′- and 3′-ketonucleosides. The first isolation of a purine 2′-deoxy-3′-ketonucleoside derivative . J. Org. Chem . 1990 , 55 , 5186 – 5188 . [CROSSREF]
  • Sanghvi , Y . S .; Ross , B .; Bharadwaj , R .; Vasseur , J.-J . An easy access of 2′,3′-dideoxy-3′-α-C-formyl-adenosine and -guanosine analogs via stereoselective C–C bond forming radical reaction . Tetrahedron Lett . 1994 , 35 , 4697 – 4700. [CROSSREF]
  • Larsen , E .; Jorgensen , P . T .; Sofan , M . A .; Pedersen , E . B . A new and easy synthesis of silylated furanoid glycals in one step from nucleosides . Synthesis 1994 , 10 , 1037 – 1038 . [CROSSREF]
  • Mikhailov , S . N .; Clercq , E . D .; Herdewijin , P . Ribosylation of pyrimidine 2′-deoxynucleosides . Nucleosides Nucleotides 1996 , 15 , 1323 – 1334 .
  • Zhang , W .; Robins , M . J . Removal of silyl protecting groups from hydroxyl functions with ammonium fluoride in methanol . Tetrahedron Lett . 1992 , 33 , 1177 – 1180 . [CROSSREF]
  • Beaton , M .; Gani , D . Synthesis of 6-amino-3,5-deoxyinositol 1-phosphates via (1R,2R,4R,6S)-1,6-epoxy-2,4-bis-benzyloxycyclohexane aminolysis in aqueous ytterbium triflate solution . Tetrahedron Lett . 1998 , 39 , 8549 – 8552 . [CROSSREF]
  • Kopylova , T . M .; Popov , S . I .; Braude , E . V .; Andrievskii , A . M . Bromination of 9,10-anthraquinone . Russ. J. Org. Chem . 1993 , 29 , 898 .
  • Carothers , W . H .; Collins , A . M .; Kirby , J . E . Acetylene polymers and their derivatives. IV. The addition of hydrogen bromide to vinylacetylene, bromoprene and dibromobutene . J. Am. Chem. Soc . 1933 , 55 , 786 – 788 .
  • Popov , S . I .; Kopylova , T . M .; Andrievskii , A . M .; Medvedev , S . V .; Yatsenko , A . V . Bromination of 2-benzoylbenzoic acids . Russ. J. Org. Chem . 1994 , 30 , 279 – 285 .
  • Hissler , M .; Harriman , A .; Khatyr , A .; Ziessel , R . Intramolecular triplet energy transfer in pyrene-metal polypyridine dyads: a strategy for extending the triplet lifetime of the metal complex . Chem. Eur. J . 1999 , 5 , 3366 – 3381 . [CROSSREF]
  • Coulson , D . R . Tetrakis(triphenylphosphine)palladium(0) . Inorg. Syn . 1972 , 13 , 121 – 124 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.